Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

ABSTRACT

The present invention provides the compound represented by Formula 1, an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and electronic device thereof, and by comprising the compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electronic device can be lowered, and the luminous efficiency and life time of the organic electronic device can be improved.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority from and the benefit under 35U.S.C. § 119 to § 121, and § 365 of Korean Patent Application No.10-2017-0127656, filed on Sep. 29, 2017, Korean Patent Application No.10-2018-0017403, filed on Feb. 13, 2018, which is hereby incorporated byreference for all purposes as if fully set forth herein. Further, thisapplication claims the benefit of priority in countries other than U.S.,which is hereby incorporated by reference herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements comprising the same, and electronicdevices thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer has a multi-layered structure havingrespectively different materials in order to improve efficiency andstability of an organic electric element, and for example, may include ahole injection layer, a hole transport layer, a light emitting layer, anelectron transport layer, an electron injection layer, or the like.

Materials used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Further, the light emitting material may be divided into a highmolecular weight type and a low molecular weight type according to itsmolecular weight, and may also be divided into a fluorescent materialderived from excited singlet states of electron and a phosphorescentmaterial derived from excited triplet states of electron according toits light emitting mechanism. Further, the light emitting material maybe divided into blue, green, and red light emitting material and yellowand orange light emitting material required for better natural colorreproduction according to its light emitting color.

Meanwhile, when only one material is used as a light emitting material,there occur problems of shift of a maximum luminescence wavelength to alonger wavelength due to intermolecular interactions and lowering of theefficiency of a corresponding element due to a deterioration in colorpurity or a reduction in luminous efficiency. On account of this, ahost/dopant system may be used as the light emitting material in orderto enhance the color purity and increase the luminous efficiency throughenergy transfer. This is based on the principle that if a small amountof dopant having a smaller energy band gap than a host forming a lightemitting layer is mixed in the light emitting layer, then excitonsgenerated in the light emitting layer are transported to the dopant,thus emitting light with high efficiency. With regard to this, since thewavelength of the host is shifted to the wavelength band of the dopant,light having a desired wavelength can be obtained according the type ofthe dopant.

Currently, the power consumption is required more than more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and life span issue also is solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase. However, efficiency cannot be maximized only bysimply improving the organic material layer. This is because long lifespan and high efficiency can be simultaneously achieved when an optimalcombination of energy levels and T₁ values, inherent material properties(mobility, interfacial properties, etc.), and the like among therespective layers included in the organic material layer is given.

Therefore, it is required to develop a light emitting material that hashigh thermal stability and can achieve efficiently a charge balance inthe light-emitting layer. That is, in order to allow an organic electricelement to fully exhibit excellent features, it should be prerequisiteto support a material constituting an organic material layer in theelement, for example, a hole injection material, a hole transportmaterial, a light emitting material, an electron transport material, anelectron injection material, or the like, by a stable and efficientmaterial. However, the stable and efficient material of organic materiallayer for an organic electronic element has not been fully developedyet, and it the development of organic material layer materials fororganic electric devices has not been sufficiently achieved.

Object, Technical Solution and Effects of the Invention

The present invention is to provide a compound lowering a drivingvoltage, improving luminous efficiency, color purity, stability andlifetime of the element, an organic electric element comprising thesame, and an electronic device thereof.

In an aspect of the present invention, the present invention providesthe compound represented by the following formula.

In another aspect of the present invention, the present inventionprovides an organic electric element using the compound represented byformula above and an electric device thereof.

By using the compound according to embodiments of the present invention,a driving voltage can be lowered and the luminous efficiency, colorpurity, stability and lifetime of the element can be largely improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrate an example of an organic electroluminescent elementaccording to the present invention: 100 is organic electric element, 110is substrate, 120 is first electrode, 130 is hole injection layer, 140is hole transport layer, 141 is buffer layer, 150 is light emittinglayer, 151 is emission-auxiliary layer, 160 is electron transport layer,170 is electron injection layer, and 180 is second electrode.

FIG. 2 shows a comparison of the energy levels of the comparativeexample compounds and the inventive example compounds.

FIG. 3 shows a band gap of the comparative example compound and theinventive example compound.

DETAILED DESCRIPTION

In the present description, a ‘group name’ corresponding to an arylgroup, an arylene group, a heterocyclic group, and the like exemplifiedfor each symbol and its substituent may be written in the name offunctional group reflecting the valence, and may also be described underthe name of a parent compound. For example, in the case of phenanthrenewhich is a kind of aryl group, it may be described by distinguishingvalence such as ‘phenanthryl (group)’ when it is ‘monovalent group’, andas ‘phenanthrylene (group)’ when it is ‘divalent group’, and it may alsobe described as aparent compound name, ‘phenanthrene’, regardless of itsvalence. Similarly, in the case of pyrimidine, it may be described as‘pyrimidine’ regardless of its valence, and it may also be described asthe name of corresponding functional group such as pyrimidinyl (group)when it is ‘monovalent group’, and as ‘pyrimidylene (group)’ when it is‘divalent group’.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein meansunivalent or bivalent functional group inwhichR, R′ and R″ are all hydrogen in the following structure,“substituted fluorenyl group” or “substituted fluorenylene group” meansthat at least any one of R, R′ and R″ is a substituent other thanhydrogen, and it comprises spiro compound formed by linking R and R′together with the carbon bonded to them.

Unless otherwise stated, the term “spiro compound” as used herein has, aspiro union which means union having one atom as the only common memberof two rings. The common atom is designated as ‘spiro atom’. Thecompounds are defined as ‘monospiro’, ‘dispiro-’ or ‘trispiro-’depending on the number of spiro atoms in one compound.

The term “heterocyclic group” as used herein means a ring comprising aheteroatom like N, O, S, P, Si or the like, it comprises a non-aromaticring as well as an aromatic ring like “heteroaryl group” or“heteroarylene group” and the compound comprising heteroatom group likeSO₂, P═O or the like instead of carbon consisting of a ring such as thefollowing compound.

Otherwise specified, the formulas used in the present invention are asdefined in the index definition of the substituent of the followingformula:

Wherein, the substituent R¹ is absent when a is an integer of zero, thesole R¹ is bonded to any one of the carbon atoms constituting thebenzene ring when a is an integer of 1, when a is an integer of 2 or 3,the substituent Ws may be bonded as follows and the substituents R¹s maybe the same or different each other, and the substituent Ws may bebonded to the carbon of the benzene ring in a similar manner when a isan integer of 4 to 6. Herein, the indication of the hydrogen bonded tothe carbon which forms the benzene ring is omitted.

The FIG. 1 illustrates an organic electric element according to anembodiment of the present invention.

Referring to the FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer formed between the first electrode 120 and the secondelectrode 180 and comprising the compound of the present invention.Here, the first electrode 120 may be an anode (positive electrode), andthe second electrode 180 may be a cathode (negative electrode). In thecase of an inverted organic electric element, the first electrode may bea cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, ahole transport layer 140, a light emitting layer 150, an electrontransport layer 160, and an electron injection layer 170 formed insequence on the first electrode 120. Here, at least one layer of theorganic material layer may be omitted, or the organic material layer mayfurther include a hole blocking layer, an electron blocking layer, anemission-auxiliary layer 151, an electron transport auxiliary layer, abuffer layer 141, etc., and the electron transport layer 160 or the likemay serve as the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include a protectivelayer or a layer for improving luminous efficiency formed on at leastone side of sides of the first electrode and the second electrode,wherein at least one side is not facing the organic material layer.

The inventive compound employed in the organic material layer may beused as a material of a hole injection layer 130, a hole transport layer140, an emission-auxiliary layer 151, an electron transport auxiliarylayer, an electron transport layer 160, an electron injection layer 170and the like, as a host or a dopant material of a light emitting layer150, or as a material of a layer for improving luminous efficiency. Forexample, the inventive compound may be used as material of the lightemitting layer 150, preferably, as host material of the light emittinglayer 150.

On the other hand, even if the core is the same core, the band gap, theelectrical characteristics, the interface characteristics, and the likemay be different depending on which substituent is bonded at whichposition. Therefore, it is necessary to study the selection of the coreand the combination of the core and the sub-substituent bonded to thecore. Specially, long life span and high efficiency can besimultaneously achieved when the optimal combination of energy levelsand T₁ values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers of anorganic material layer is achieved.

Therefore, according to the present invention, energy level and T₁ valuebetween the respective layers of the organic material layer, inherentmaterial properties (mobility, interfacial properties, etc.) and thelike can be optimized by using as a host material of a light emittinglayer a single compound represented by the Formula 1 or a mixture of thecompound represented by the Formula 1 and the compound represented bythe Formula 15, and thus it is possible to simultaneously improve thelife span and efficiency of the organic electric element.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 120, forming the organic material layer including the holeinjection layer 130, the hole transport layer 140, the light emittinglayer 150, the electron transport layer 160, and the electron injectionlayer 170 thereon, and then depositing a material, which can be used asthe cathode 180, thereon. Also, an emitting auxiliary layer 151 may beformed between a hole transport layer 140 and a light emitting layer150, and an electron transport auxiliary layer may be formed between alight emitting layer 150 and an electron transport layer 160.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transfer,instead of deposition. Since the organic material layer according to thepresent invention may be formed in various ways, the scope of protectionof the present invention is not limited by a method of forming theorganic material layer.

Also, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode, anorganic solar cell, an organic photo conductor, an organic transistor,and an element for monochromatic or white illumination.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, the compound according to an aspect of the presentinvention will be described.

The compound according to an aspect of the present invention isrepresented by formula 1 below.

In the formula 1, each of symbols may be defined as follows.

In Formula 1, X¹ and X² are each independently O or S. For example, bothX¹ and X² are O or S, is O and X² is S, or X¹ is S and X² is O.Preferably, X¹ is S and X² is O.

Ar¹ to Ar³ are each independently a C₆-C₆₀ aryl group, preferably, aC₆-C₃₀ or a C₆-C₂₀ aryl group, more preferably a C₆-C₁₈ aryl group, forexample, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl,triphenylene, pyrene or the like.

R¹ to R⁵ are each independently selected from the group consisting ofhydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenyl group, aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphaticring, a fused ring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and-L′-N(R_(a))(R_(b)).

In addition, adjacent R¹ groups to adjacent R⁵ groups may be optionallylinked to each other to form a ring. Here, the ring is selected from thegroup consisting of a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic group,a C₃-C₆₀ aliphatic ring, and a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring.

Here, “adjacent groups connected to each other” means that adjacent R¹s,adjacent R²s, adjacent R³s, adjacent R⁴s, or adjacent R⁴s arerespectively connected to each other.

a and b are each an integer of 0 to 3, c, d, e, l and m are each aninteger of 0 to 4, and n is an integer of 0 to 5, provided that e+l andd+m are integers of 4 or less, respectively. When each of these is aninteger of 2 or more, each of R¹s, each of R²s, each of R³s, each ofR⁴s, each of R⁵s, each of Ar¹s, each of Ar³s is the same or differentfrom each other.

When R¹ to R⁵ are each an aryl group, R¹ to R⁵ may be preferably aC₆-C₃₀ or a C₆-C₂₀ aryl group, more preferably a C₆-C₁₈ aryl group, forexample, phenyl, biphenyl, naphthyl, terphenyl or the like.

When adjacent Ws, adjacent R²s, adjacent R³, adjacent R⁴, or adjacent R⁵are linked to each other to form a ring, preferably a C₆-C₂₀ aromaticring group may be formed, for example, benzene rings, naphthalene,phenanthrene or the like may be formed.

L′ is selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a C₃-C₆₀ aliphatic ring and a fused ring groupformed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

R_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring and afused ring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring.

Ar¹ to Ar³, R¹ to R⁵, L′, R_(a), R_(b), and a ring formed by bondingneighboring groups of R¹ to R⁵ to each other may be each furthersubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aphosphine oxide group unsubstituted or substituted with a C₁-C₂₀ alkylgroup or a C₆-C₂₀ aryl group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxylgroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted withdeuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a C₃-C₂₀ cycloalkyl group, a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, a C₇-C₂₀ arylalkyl group,and a C₈-C₂₀ arylalkenyl group.

That is, when Ar¹ to Ar³, R¹ to R⁵, L′, R_(a), R_(b), and a ring formedby bonding neighboring groups of R¹ to R⁵ to each other are each an arylgroup, an arylene group, an aromatic hydrocarbon, a fluorenyl group, afluorenylene group, a heterocyclic group, an aliphatic ring (group), afused ring (group), an alkyl group, an alkenyl group, an alkynyl group,an alkoxy group, an aryloxy group and the like, each of these may befurther substituted with one or more substituents selected from thegroup above.

For example, when Ar¹ to Ar³, R¹ to R⁵, L′, R_(a), R_(b), and a ringformed by bonding neighboring groups of R¹ to R⁵ to each other may befurther substituted with an aryl group, preferably a C₆-C₂₀ aryl group,more preferably, a C₆-C₁₈ aryl group, for example, phenyl, naphthyl,biphenyl, terphenyl, and the like.

Also, when Ar¹ to Ar³, R¹ to R⁵, L′, R_(a), R_(b), and a ring formed bybonding neighboring groups of R¹ to R⁵ to each other are furthersubstituted with deuterium or F.

Formula 1 may be represented by one of the following Formula 2 toFormula 5.

In Formulas 2 to 5, Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, l, m and n arethe same as defined in Formula 1.

In addition, Formula 1 may be represented by one of Formula 6 to Formula8.

In Formulas 6 to 8, X¹, X², Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, l and mare the same as defined in Formula 1.

In addition, Formula 1 may be represented the following Formula 9 orFormula 10.

In Formula 9 and 10, X¹, X², Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, m andn are the same as defined in Formula 1.

In addition, Formula 1 may be represented by one of Formula 11 toFormula 13.

In Formulas 11 to 13, X¹, X², Ar¹ to Ar³, R¹, R², R⁴, R⁵, a, b, d, e, l,m and n are the same as defined in Formula 1.

In addition, Formula 1 may be represented by Formula 14:

In Formula 14, X¹, X², Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, l and m arethe same as defined in Formula 1.

Preferably, in Formula 1, at least one of Ar¹, Ar³ and R³ is a C₆-C₂₄aryl group, more preferably, Ar¹ or Ar³ is a C₆-C₂₄ aryl group, and morepreferably, R³ is a C₆-C₂₄ aryl group.

Specifically, the compound represented by formula 1 may be one of thefollowing compounds, but it is not limited thereto.

In another aspect of the present invention, the present inventionprovides an organic electric element comprising a first electrode, asecond electrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises compound represented by Formula 1. The organic material layercomprises at least one layer of a hole injection layer, a hole transportlayer, an emission-auxiliary layer, a light emitting layer, an electrontransport auxiliary layer, an electron transport layer and an electroninjection layer, at least one layer of the organic material layerscomprises a single compound or a mixture of two or more kindsrepresented by Formula 1.

Preferably, the compound represented by Formula 1 is comprised in thelight emitting layer.

Also, preferably, the light emitting layer may be further comprisecompound represented by Formula 15.

In Formula 15, each of symbols may be defined as follows.

Z¹ to Z⁴, Z¹³ to Z¹⁶ are independently C(R) or N, Z⁵ to Z¹² areindependently C, C(R) or N.

L² is selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a C₃-C₆₀ aliphatic ring and a fused ring groupformed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

When L² is an arylene group, L² may be preferably a C₆-C₃₀ or C₆-C₂₀arylene group, more preferably a C₆-C₁₈ arylene group, for example,phenylene, naphthalene, biphenyl, terphenyl or the like. When L² is aheterocyclic group, L² may be preferably a C₂-C₃₀ or C₂-C₂₀ heterocyclicgroup, more preferably a C₂-C₁₈ heterocyclic group, for example,carbazole, phenylcarbazole or the like.

W is N(Ar⁵), O, S or C(R′)(R″).

Ar⁴ and Ar⁵ are each independently selected from the group consisting ofa C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a C₃-C₆₀ aliphatic ring, a fused ring group formedby a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxylgroup, a C₆-C₃₀ aryloxy group, -L′-N(R_(a))(R_(b)) and a combinationthereof. Here, the term “combination of these” means, for example, acombination of an aryl group and a heterocyclic group, a combination ofan aryl group and an aliphatic ring, a combination of a heterocyclicgroup and an aliphatic ring group, and the like.

When Ar⁴ and Ar⁵ are each an aryl group, Ar⁴ and Ar⁵ may be preferably aC₆-C₃₀ or C₆-C₂₀ aryl group, more preferably a C₆-C₁₈ aryl group, forexample, phenyl, naphthyl, biphenyl, terphenyl or the like. When Ar⁴ andAr⁵ are each a heterocyclic group, Ar⁴ and Ar⁵ may be preferably aC₂-C₃₀ or a C₂-C₂₀ heterocyclic group, more preferably a C₂-C₁₈heterocyclic group, for example, triazine, pyrimidine, pyridine,quinazoline, carbazole, phenylcarbazole, dibenzothiophene, dibenzofuranor the like.

R, R′ and R″ are each independently selected from the group consistingof hydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenyl group,a C₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphaticring, a fused ring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and-L′-N(R_(a))(R_(b)).

In addition, adjacent R groups may be optionally linked to each other toform a ring, and R′ and R″ may be optionally linked to each other toform a ring. The ring formed by linking between adjacent R¹ groups,between R′ and R″ may be a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclicgroup, a C₃-C₆₀ aliphatic ring, or a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, preferably, a C₆-C₂₀aromatic ring group, or a C₂-C₂₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si, and P,more preferably, a C₆-C₁₀ aromatic ring group, or a C₂-C₁₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P, for example, benzene ring,naphthalene, phenanthrene, thiophene, benzothiophene, pyridine and thelike.

L′, R_(a) and R_(b) are the same as defined in Formula 1.

L², Ar⁴, Ar⁵, R, R′, R″, a ring formed by linking between adjacent Rgroups, and a ring formed by linking between R′ and R″ may be eachfurther substituted with one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aphosphine oxide group unsubstituted or substituted with a C₁-C₂₀ alkylgroup or a C₆-C₂₀ aryl group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxylgroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted withdeuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a C₃-C₂₀ cycloalkyl group, a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, a C₇-C₂₀ arylalkyl group,and a C₈-C₂₀ arylalkenyl group.

Formula 15 may be represented by one of Formulas 16 to 19.

In Formulas 16 to 19, Ar⁴, Ar⁵, Z¹ to Z¹⁶, L², R′ and R″ are the same asdefined in Formula 11.

Preferably, in Formulas 16 to 19, at least one of Ar⁴ and Ar⁵ is asubstituted or unsubstituted C₆-C₃₀ aryl group aryl group, morepreferably, both Ar⁴ and Ar⁵ are a C₆-C₃₀ aryl group.

Preferably, Formula 15 may be represented by Formula 20.

In Formula 20, each of symbols may be defined as follows.

Ar⁴, Z¹ to Z¹⁶, and L² are the same as defined in Formula 11.

L¹ is selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a C₃-C₆₀ aliphatic ring and a fused ring groupformed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

When L′ is an arylene group, L′ may be preferably a C₆-C₃₀ or C₆-C₂₀arylene group, more preferably a C₆-C₁₈ arylene group, for example,phenylene, naphthalene, biphenyl or the like.

Y is O, S or N(R^(c)).

R^(a) and R^(b) are each independently selected from the groupconsisting of hydrogen, deuterium, halogen, a C₆-C₂₀ aryl group, afluorenyl group, a C₆-C₂₀ aryl group substituted with deuterium, aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkylgroup, a fused ring group formed by a C₃-C₆₀ aliphatic ring with aC₆-C₆₀ aromatic ring, a C₇-C₂₀ arylalkyl group and a C₈-C₂₀ arylalkenylgroup.

In addition, adjacent R^(a) groups or adjacent R^(a) groups may beoptionally linked to each other to form a ring, wherein the ring isselected from the group consisting of a C₆-C₆₀ aromatic ring, a C₂-C₆₀heterocyclic group, a C₃-C₆₀ aliphatic ring, and a fused ring groupformed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

R^(c) is selected from the group consisting of a C₆-C₂₀ aryl group, afluorenyl group, a C₆-C₂₀ aryl group substituted with deuterium, aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkylgroup, a fused ring group formed by a C₃-C₆₀ aliphatic ring with aC₆-C₆₀ aromatic ring and a combination thereof.

y is an integer of 0 to 3, z is an integer of 0 to 4, where each ofthese is an integer of 2 or more, each of R^(a)s, each of R^(b)s is thesame or different from each other.

Specifically, the compound represented by formula 15 may be one of thefollowing compounds, but it is not limited thereto.

Hereinafter, synthesis examples of the compounds represented by Formulas1 and 12, respectively, and preparation method of an organic electricelement according to one embodiment of the present invention will bedescribed in detail by way of examples. However, the present inventionis not limited to the following examples.

Synthesis Example Synthesis Example of Formula 1

As shown in Reaction Scheme 1 below, the compound (final product)represented by Formula 1 according to the present invention can besynthesized by reacting Sub 1 with Sub 2, but there is no limitationthereto.

Synthesis Example of Sub 1

Sub 1 of the Reaction Scheme 1 can be synthesized according to thereaction route of the following Reaction Scheme 2, but there is nolimitation thereto.

Synthesis Example of Sub 1(1)

Sub 1-1-1 (18.1 g, 80 mmol), Sub 1-2-1 (29.6 g, 80 mmol), K₂CO₃ (19.3 g,140 mmol) and Pd(PPh₃)₄ (2.8 g, 2.4 mmol) in a round bottom flask weredissolved in THF and water. The solution was refluxed at 80□ for 12hours. When the reaction was completed, the reaction product was cooledto room temperature, extracted with CH₂Cl₂ and washed with water. Theorganic layer was dried with MgSO₄ and concentrated. Thereafter, theconcentrate was applied to silica gel column to obtain 23.6 g (yield:68%) of the product.

Synthesis Example of Sub 1(16)

Sub 1-1-2 (30.3 g, 80 mmol) and Sub 1-2-2 (29.6 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,30.5 g (yield: 65%) of the product was obtained.

Synthesis Example of Sub 1(19)

Sub 1-1-3 (22.1 g, 80 mmol) and Sub 1-2-3 (35.7 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,30.9 g (69%) of the product was obtained.

Synthesis Example of Sub 1(28)

Sub 1-1-1 (18.1 g, 80 mmol) and Sub 1-2-4 (35.7 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,28.6 g (70%) of the product was obtained.

Synthesis Example of Sub 1(29)

Sub 1-1-1 (18.1 g, 80 mmol) and Sub 1-2-5 (29.6 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,23.3 g (67%) of the product was obtained.

Synthesis Example of Sub 1(35)

Sub 1-1-1 (18.1 g, 80 mmol) and Sub 1-2-6 (34.9 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,27.6 g (69%) of the product was obtained.

Synthesis Example of Sub 1(37)

Sub 1-1-1 (18.1 g, 80 mmol) and Sub 1-2-1′ (23.5 g, 80 mmol) werereacted in the same manner as in the synthesis method of Sub 1(1), as aresult, 20.0 g (70%) of the product was obtained.

The example of the compound belonging to Sub 1 may be, but not limitedto, the following compounds, and Table 1 shows FD-MS values of thefollowing compounds.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1(1) m/z = 433.10(C₂₇H₁₆ClN₃O= 433.90) Sub 1(2) m/z = 483.11(C₃₁H₁₈ClN₃O = 483.96) Sub 1(3) m/z =483.11(C₃₁H₁₈ClN₃O = 483.96) Sub 1(4) m/z = 509.13(C₃₁H₂₀ClN₃O = 509.99)Sub 1(5) m/z = 533.13(C₃₅H₂₀ClN₃O = 534.02) Sub 1(6) m/z =557.13(C₃₇H₂₀ClN₃O = 558.04) Sub 1(7) m/z = 585.16(C₃₉H₂₄ClN₃O = 586.09)Sub 1(8) m/z = 447.11(C₂₈H₁₈ClN₃O = 447.92) Sub 1(9) m/z =483.11(C₃₁H₁₈ClN₃O = 483.96) Sub 1(10) m/z = 483.11(C₃₁H₁₈ClN₃O =483.96) Sub 1(11) m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 1(12) m/z =533.13(C₃₅H₂₀ClN₃O = 534.02) Sub 1(13) m/z = 483.11(C₃₁H₁₈ClN₃O =483.96) Sub 1(14) m/z = 483.11(C₃₁H₁₈ClN₃O = 483.96) Sub 1(15) m/z =509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 1(16) m/z = 585.16(C₃₉H₂₄ClN₃O =586.09) Sub 1(17) m/z = 583.15(C₃₉H₂₂ClN₃O = 584.08) Sub 1(18) m/z =533.13(C₃₅H₂₀ClN₃O = 534.02) Sub 1(19) m/z = 559.15(C₃₇H₂₂ClN₃O =560.05) Sub 1(20) m/z = 585.16(C₃₉H₂₄ClN₃O = 586.09) Sub 1(21) m/z =509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 1(22) m/z = 633.16(C₄₃H₂₄ClN₃O =634.14) Sub 1(23) m/z = 609.16(C₄₁H₂₄ClN₃O = 610.11) Sub 1(24) m/z =501.10(C₃₁H₁₇ClFN₃O = 501.95) Sub 1(25) m/z = 433.10(C₂₇H₁₆ClN₃O =433.90) Sub 1(26) m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 1(27) m/z =509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 1(28) m/z = 509.13(C₃₃H₂₀ClN₃O =509.99) Sub 1(29) m/z = 433.10(C₂₇H₁₆ClN₃O = 433.90) Sub 1(30) m/z =509.13(C₃₃H₂₀ClN₃O = 509.99) Sub 1(31) m/z = 483.11(C₃₁H₁₈ClN₃O =483.96) Sub 1(32) m/z = 499.09(C₃₁H₁₈ClN₃S = 500.02) Sub 1(33) m/z =499.09(C₃₁H₁₈ClN₃S = 500.02) Sub 1(34) m/z = 549.11(C₃₅H₂₀ClN₃S =550.08) Sub 1(35) m/z = 499.09(C₃₁H₁₈ClN₃S = 500.02) Sub 1(36) m/z =575.12(C₃₇H₂₂ClN₃S = 576.11) Sub 1(37) m/z = 357.07(C₂₁H₁₂ClN₃O =357.80)

Synthesis Example of Sub 2

Sub 2 of the Reaction Scheme 1 can be synthesized according to thereaction route of the following Reaction Scheme 3, but there is nolimitation thereto.

Synthesis Example of Sub 2(3)

Synthesis of Sub 2-3-1

Sub 2-1-1 (24.8 g, 80 mmol) and Sub 2-2-1 (22.5 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,20.6 g (yield: 76%) of the product was obtained.

Synthesis Example of Sub 2(3)

After dissolving Sub 2-3-1 (4.7 g, 14 mmol) in DMF (98 mL),bispinacolborate (3.6 g, 15 mmol), PdCl₂(dppf) catalyst (0.3 g, 0.4mmol), KOAc (4.1 g, 42 mmol)) were added in order and the mixture wasstirred for 24 hours. Thereafter, the mixed solution was passed througha silica gel column and recrystallized to obtain 3.9 g (yield: 72%) ofthe borate compound Sub 2 (3).

Synthesis Example of Sub 2(23)

Synthesis of Sub 2-3-2

Sub 2-1-1 (24.8 g, 80 mmol) and Sub 2-2-2 (28.7 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,25.3 g (76%) of the product was obtained.

Synthesis of Sub 2(23)

Sub 2-3-2 (5.8 g, 14 mmol) and bispinacolborate (3.6 g, 15 mmol) werereacted in the same manner as in the synthesis method of Sub 2(3), as aresult, 4.6 g (71%) of the product Sub 2(23) was obtained.

Synthesis Example of Sub 2(28)

Synthesis of Sub 2-3-3

Sub 2-1-1 (24.8 g, 80 mmol) and Sub 2-2-3 (34.8 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,29.1 g (74%) of the product was obtained.

Synthesis of Sub 2(28)

Sub 2-3-3 (6.9 g, 14 mmol) and bispinacolborate (3.6 g, 15 mmol) werereacted in the same manner as in the synthesis method of Sub 2(3), as aresult, 5.1 g (68%) of the product Sub 2(28) was obtained.

Synthesis Example of Sub 2(31)

Synthesis of Sub 2-3-4

Sub 2-1-2 (23.5 g, 80 mmol) and Sub 2-2-4 (25.0 g, 80 mmol) were reactedin the same manner as in the synthesis method of Sub 1(1), as a result,22.7 g (71%) of the product was obtained.

Synthesis of Sub 2(31)

Sub 2-3-4 (5.6 g, 14 mmol) and bispinacolborate (3.6 g, 15 mmol) werereacted in the same manner as in the synthesis method of Sub 2(3), as aresult, 4.4 g (70%) of the product Sub 2(31) was obtained.

The example of the compound belonging to Sub 2 may be, but not limitedto, the following compounds, and Table 2 shows FD-MS values of thefollowing compounds.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2(1) m/z = 386.15(C₂₄H₂₃BO₂S =386.32) Sub 2(2) m/z = 386.15(C₂₄H₂₃BO₂S = 386.32) Sub 2(3) m/z =386.15(C₂₄H₂₃BO₂S = 386.32) Sub 2(4) m/z = 538.21(C₃₆H₃₁BO₂S = 538.51)Sub 2(5) m/z = 538.21(C₃₆H₃₁BO₂S = 538.51) Sub 2(6) m/z =462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(7) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41)Sub 2(8) m/z = 538.21(C₃₆H₃₁BO₂S = 538.51) Sub 2(9) m/z =538.21(C₃₆H₃₁BO₂S = 538.51) Sub 2(10) m/z = 462.18(C₃₀H₂₇BO₂S = 467.41)Sub 2(11) m/z = 538.21(C₃₆H₃₁BO₂S = 538.51) Sub 2(12) m/z =462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(13) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41)Sub 2(14) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(15) m/z =462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(16) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41)Sub 2(17) m/z = 538.21(C₃₆H₃₁BO₂S = 538.51) Sub 2(18) m/z =538.21(C₃₆H₃₁BO₂S = 538.51) Sub 2(19) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41)Sub 2(20) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(21) m/z =462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(22) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41)Sub 2(23) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(24) m/z =462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(25) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41)Sub 2(26) m/z = 462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(27) m/z =462.18(C₃₀H₂₇BO₂S = 462.41) Sub 2(28) m/z = 538.21(C₃₆H₃₁BO₂S = 538.51)Sub 2(29) m/z = 370.17(C₂₄H₂₃BO₃ = 370.26) Sub 2(30) m/z =370.17(C₂₄H₂₃BO₃ = 370.26) Sub 2(31) m/z = 446.21(C₃₀H₂₇BO₃ = 446.35)Sub 2(32) m/z = 522.24(C₃₆H₃₁BO₃ = 522.45)

Synthesis Example of Final Product Synthesis Example of 1-1

Sub 1(1) (34.7 g, 80 mmol), Sub 2(1) (30.9 g, 80 mmol) and K₂CO₃ (19.3g, 140 mmol), Pd(PPh₃)₄ (2.8 g, 2.4 mmol) in a round bottom flask weredissolved in THF and water. The solution was refluxed at 80□ for 12hours. When the reaction was completed, the reaction product was cooledto room temperature, extracted with CH₂Cl₂ and washed with water. Theorganic layer was dried with MgSO₄ and concentrated. Thereafter, theconcentrate was applied to silica gel column to obtain 37.4 g (yield:71%) of the product.

Synthesis Example of 1-6

Sub 1(6) (44.6 g, 80 mmol) and Sub 2(2) (30.9 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 43.2g (yield: 69%) of the product was obtained.

Synthesis Example of 1-12

Sub 1(12) (42.7 g, 80 mmol) and Sub 2(33) (34.9 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 42.7g (yield: 66%) of the product was obtained.

Synthesis Example of 1-33

Sub 1(27) (40.8 g, 80 mmol) and Sub 2(9) (43.1 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 51.0g (yield: 72%) of the product was obtained.

Synthesis Example of 1-44

Sub 1(28) (40.8 g, 80 mmol) and Sub 2(10) (37.0 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 45.4g (yield: 70%) of the product was obtained.

Synthesis Example of 1-53

Sub 1(34) (44.0 g, 80 mmol) and Sub 2(29) (29.6 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 41.2g (yield: 68%) of the product was obtained.

Synthesis Example of 1-64

Sub 1(37) (48.2 g, 80 mmol) and Sub 2(34) (34.9 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 45.6g (yield: 71%) of the product was obtained.

Synthesis Example of 1-75

Sub 1(25) (34.7 g, 80 mmol) and Sub 2(35) (41.8 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 46.4g (yield: 73%) of the product was obtained.

Synthesis Example of 2-1

Sub 1(1) (34.7 g, 80 mmol) and Sub 2(27) (37.0 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 42.3g (yield: 72%) of the product was obtained.

Synthesis Example of 2-22

Sub 1(38) (50.7 g, 80 mmol) and Sub 2(24) (37.0 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 51.6g (yield: 69%) of the product was obtained.

Synthesis Example of 2-33

Sub 1(27) (40.8 g, 80 mmol) and Sub 2(36) (49.2 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 53.9g (yield: 70%) of the product was obtained.

Synthesis Example of 2-40

Sub 1(25) (34.7 g, 80 mmol) and Sub 2(37) (43.1 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 44.7g (yield: 69%) of the product was obtained.

Synthesis Example of 2-51

Sub 1(33) (36.0 g, 80 mmol) and Sub 2(38) (35.7 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 41.1g (yield: 70%) of the product was obtained.

Synthesis Example of 2-55

Sub 1(39) (42.1 g, 80 mmol) and Sub 2(23) (37.0 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 44.9g (yield: 68%) of the product was obtained.

Synthesis Example of 2-58

Sub 1(25) (34.7 g, 80 mmol) and Sub 2(39) (47.9 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 45.9g (yield: 66%) of the product was obtained.

Synthesis Example of 3-10

Sub 1(37) (28.6 g, 80 mmol) and Sub 2(10) (37.0 g, 80 mmol) were reactedin the same manner as in the synthesis method of 1-1, as a result, 38.9g (yield: 74%) of the product was obtained.

The FD-MS values of the compounds 1-1 to 1-84, 2-60 to 2-60 and 3-1 to3-36 of the present invention prepared according to the above synthesisexamples are shown in Table 3 below.

TABLE 3 Compound FD-MS Compound FD-MS H m/z = 657.19(C₄₅H₂₇N₃OS =657.79) 1-2 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1-3 m/z =707.20(C₄₉H₂₉N₃OS = 707.85) 1-4 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1-5m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-6 m/z = 781.22(C₅₅H₃₁N₃OS = 781.93)1-7 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1-8 m/z = 721.22(C₅₀H₃₁N₃OS =721.88) 1-9 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1-10 m/z =707.20(C₄₉H₂₉N₃OS = 707.85) 1-11 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-12m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1-13 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85)1-14 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1-15 m/z = 733.22(C₅₁H₃₁N₃OS =733.89) 1-16 m/z = 859.27(C₆₁H₃₇N₃OS = 860.05) 1-17 m/z =807.23(C₅₇H₃₃N₃OS = 807.97) 1-18 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-19m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1-20 m/z = 859.27(C₆₁H₃₇N₃OS = 860.05)1-21 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-22 m/z = 857.25(C₆₁H₃₅N₃OS =858.03) 1-23 m/z = 833.25(C₅₉H₃₅N₃OS = 834.01) 1-24 m/z =825.23(C₅₇H₃₂FN₃OS = 825.96) 1-25 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1-26m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-27 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99)1-28 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1-29 m/z = 732.22(C₅₁H₃₁N₃OS =733.89) 1-30 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-31 m/z =657.19(C₄₅H₂₇N₃OS = 657.79) 1-32 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1-33m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 1-34 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89)1-35 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-36 m/z = 809.25(C₅₇H₃₅N₃OS =809.99) 1-37 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-38 m/z =733.22(C₅₁H₃₁N₃OS = 733.89) 1-39 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1-40m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1-41 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95)1-42 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-43 m/z = 733.22(C₅₁H₃₁N₃OS =733.89) 1-44 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1-45 m/z =809.25(C₅₇H₃₅N₃OS = 809.99) 1-46 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1-47m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 1-48 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95)1-49 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1-50 m/z = 707.20(C₄₉H₂₉N₃OS =707.85) 1-51 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1-52 m/z =783.23(C₅₅H₃₃N₃OS = 783.95) 1-53 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-54m/z = 781.22(C₅₅H₃₁N₃OS = 781.93) 1-55 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99)1-56 m/z = 721.22(C₅₀H₃₁N₃OS = 721.88) 1-57 m/z = 707.20(C₄₉H₂₉N₃OS =707.85) 1-58 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1-59 m/z =733.22(C₅₁H₃₁N₃OS = 733.89) 1-60 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1-61m/z = 723.18(C₄₉H₂₉N₃S₂ = 723.91) 1-62 m/z = 723.18(C₄₉H₂₉N₃S₂ = 723.91)1-63 m/z = 749.20(C₅₁H₃₁N₃S₂ = 749.95) 1-64 m/z = 875.24 (C₆₁H₃₇N₃S₂ =876.11) 1-65 m/z = 823.21(C₅₇H₃₃N₃S₂ = 824.03) 1-66 m/z = 773.20(C₅₃H₃₁N₃S₂ = 773.9 7) 1-67 m/z = 799.21(C₅₅H₃₃N₃S₂ = 800.01) 1-68 m/z =875.24(C₆₁H₃₇N₃S₂ = 876.11) 1-69 m/z = 749.20(C₅₁H₃₁N₃S₂ = 749.95) 1-70m/z = 873.23(C₆₁H₃₅N₃S₂ = 874.09) 1-71 m/z = 849.23(C₅₉H₃₅N₃S₂ = 850.07)1-72 m/L = 791.19(C₅₃H_(30F)N₃S₂ = 791.96) 1-73 m/z = 641.21(C₄₅H₂₇N₃O₂= 641.73) 1-74 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 1-75 m/z =798.30(C₅₇H₃₀D₅N₃O₂ = 799.0) 1-76 m/z = 843.29 (C₆₁H₃₇N₃O₂ = 843.99)1-77 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 1-78 m/z = 717.24(C₅₁H₃₁N₃O₃ =717.83) 1-79 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 1-80 m/z =793.27(C₅₇H₃₅N₃O₂ = 793.93) 1-81 m/z = 869.30(C₆₃H₃₉N₃O₂ = 870.02) 1-82m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 1-83 m/z = 722.27(C₅₁H₂₆D₅N₃O₂ =722.9) 1-84 m/z = 793.27(C₅₇H₃₅N₃O₂ = 793.93) 2-1 m/z =733.22(C₅₁H₃₁N₃OS = 733.89) 2-2 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-3m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-4 m/z = 859.27(C₆₁H₃₇N₃OS = 860.05)2-5 m/z = 833.25(C₅₉H₃₅N₃OS = 834.01) 2-6 m/z = 857.25(C₆₁H₃₅N₃OS =858.03) 2-7 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-8 m/z = 797.25(C₅₆H₃₅N₃OS = 79 7.98) 2-9 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-10m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-11 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99)2-12 m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) 2-13 m/z = 783.23(C₅₅H₃₃N₃OS =783.95) 2-14 m/z = 783.23(C₅₅H₃₃NN₃OS = 783.95) 2-15 m/z =809.25(C₅₇H₃₅N₃OS = 809.99) 2-16 m/z = 935.30(C₆₇H₄₁N₃OS = 936.15) 2-17m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) 2-18 m/z = 833.25(C₅₉H₃₅N₃OS = 834.01)2-19 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-20 m/z = 909.28(C₆₅H₃₉N₃OS =910.11) 2-21 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-22 m/z =933.28(C₆₇H₃₉N₃OS = 934.13) 2-23 m/z = 909.28(C₆₅H₃₉N₃OS = 910.11) 2-24m/z = 851.24 (C₅₉H₃₄FN₃OS = 852.00) 2-25 m/z = 733.22(C₅₁H₃₁N₃OS =733.89) 2-26 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-27 m/z =885.28(C₆₃H₃₉N₃OS = 886.09) 2-28 m/z = 935.30(C₆₇H₄₁N₃OS = 936.15) 2-29m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-30 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99)2-31 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 2-32 m/z = 885.28(C₆₃H₃₉N₃OS =886.09) 2-33 m/z = 961.31(C₆₉H₄₃N₃OS = 962.18) 2-34 m/z =809.25(C₅₇H₃₅N₃OS = 809.99) 2-35 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-36m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-37 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09)2-38 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-39 m/z = 961.31(C₆₉H₄₃N₃OS =962.18) 2-40 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-41 m/z =885.28(C₆₃H₃₉N₃OS = 886.09) 2-42 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-43m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-44 m/z = 1032.40(C₇₄H₅₄N₃OS =1033.33) 2-45 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-46 m/z =885.28(C₆₃H₃₉N₃OS = 886.09) 2-47 m/z = 961.31(C₆₉H₄₃N₃OS = 962.18) 2-48m/z = 859.27(C₆₁H₃₇N₃OS = 860.08) 2-49 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99)2-50 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-51 m/z = 733.22(C₅₂H₃₂N₃OS =733.89) 2-52 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-53 m/z =977.29(C₆₉H₄₃N₃S₂ = 978.24) 2-54 m/z = 825.23(C₅₇H₃₅N₃S₂ = 826.05) 2-55m/z = 825.23(C₅₇H₃₅N₃S₂ = 826.05) 2-56 m/z = 901.26(C₆₃H₃₉N₃S₂ = 902.15)2-57 m/z = 869.30(C₆₃H₃₉N₃O₂ = 870.02) 2-58 m/z = 869.30(C₆₃H₃₉N₃O₂ =870.02) 2-59 m/z = 945.34(C₆₉H₄₃N₃O₂ = 946.12) 2-60 m/z =809.25(C₅₇H₃₅N₃OS = 809.99) 3-1 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-2m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-3 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69)3-4 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 3-5 m/z = 631.17(C₄₃H₂₅N₃OS =631.75) 3-6 m/z = 731.20(C₅₂H₂₉N₃OS = 731.87) 3-7 m/z =581.16(C₃₉H₂₃N₃OS = 581.69) 3-8 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-9m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-10 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79)3-11 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-12 m/z = 733.22(C₅₂H₃₂N₃OS =733.89) 3-13 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 3-14 m/z =581.16(C₃₉H₂₃N₃OS = 581.69) 3-15 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-16m/z = 799.21(C₅₅H₃₃N₃S₂ = 800.01) 3-17 m/z = 647.15(C₄₃H₂₅N₃S₂ = 647.81)3-18 m/z = 747.18(C₅₁H₂₉N₃S₂ = 747.93) 3-19 m/z = 565.18(C₃₉H₂₃N₃O₂ =565.63) 3-20 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 3-21 m/z =722.27(C₅₁H₂₆D₅N₃S₂ = 722.86) 3-22 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79)3-23 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-24 m/z = 707.20(C₄₉H₂₉N₃OS =707.85) 3-25 m/z = 733.22(C₅₂H₃₂N₃OS = 733.89) 3-26 m/z =707.20(C₄₉H₂₉N₃OS = 707.85) 3-27 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 3-28m/z = 859.27(C₆₂H₃₇N₃OS = 860.05) 3-29 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79)3-30 m/z = 733.22(C₅₂H₃₂N₃OS = 733.89) 3-31 m/z = 809.25(C₅₇H₃₅N₃OS =809.99) 3-32 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 3-33 m/z =885.28(C₆₃H₃₉N₃OS = 886.09) 3-34 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 3-35m/z = 673.16(C₄₅H₂₇N₃S₂ = 673.85) 3-36 m/z = 793.27(C₅₇H₃₅N₃O₂ = 793.93)

Synthesis Example of Formula 11

As shown in the reaction Scheme 4, the compound (final products)represented by Formula 11 according to the present invention can besynthesized by reacting Sub 3 with Sub 4, but there is no limitationthereto.

Synthesis Example of 4-1

After 3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved inTHF, (9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazol-3-yl)boronic acid(8.8 g, 20 mmol), Pd(PPh₃)₄ (0.03 eq,), K₂CO₃(3 eq.) and water wereadded thereto and the solution was stirred under reflux. When thereaction was completed, the reaction product was extracted with etherand water. The organic layer was dried with MgSO₄ and concentrated.Thereafter, the concentrate was applied to silica gel column to obtain9.2 g (yield: 72%) of the product.

Synthesis Example of Synthesis Example of 4-21

10-bromo-7-(pyridin-2-yl)-7H-benzo[c]carbazole (7.5 g, 20 mmol) anddibenzo[b,d]furan-2-ylboronic acid (4.2 g, 20 mmol) were reacted in thesame manner as in the synthesis method of 4-1, as a result, 6.5 g(yield: 71%) of the product was obtained.

Synthesis Example of 4-25

9-([1,1′-biphenyl]-4-yl)-3-bromo-9H-carbazole (8.0 g, 20 mmol) and(9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.7 g, 20 mmol) werereacted in the same manner as in the synthesis method of 4-1, as aresult, 9.2 g (yield: 75%) of the product was obtained.

Synthesis Example of 4-31

3′-bromo-9-phenyl-9H-2,9′-bicarbazole (9.7 g, 20 mmol) and(9-phenyl-9H-carbazol-3-yl)boronic acid (5.7 g, 20 mmol) were reacted inthe same manner as in the synthesis method of 4-1, as a result, 9.5 g(yield: 73%) of the product was obtained.

Synthesis Example of 4-32

3-bromo-9-(dibenzo[b,d]furan-2-yl)-9H-carbazole (8.2 g, 20 mmol) and(12-([1,1′:4′,1″-terphenyl]-4-yl)-12H-benzo[4,5]thieno[2,3-a]carbazol-3-yl)boronicacid (10.9 g, 20 mmol) were reacted in the same manner as in thesynthesis method of 4-1, as a result, 11.5 g (yield: 69%) of the productwas obtained.

Synthesis Example of 4-34

4-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) and(4-(dibenzo[b,d]thiophen-3-yl)phenyl)boronic acid (6.1 g, 20 mmol) werereacted in the same manner as in the synthesis method of 4-1, as aresult, 6.7 g (yield: 67%) of the product was obtained.

Synthesis Example of 4-35

3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) and9(9,9-dimethyl-9H-fluoren-3-yl)boronic acid (4.8 g, 20 mmol) werereacted in the same manner as in the synthesis method of 4-1, as aresult, 6.1 g (yield: 70%) of the product was obtained.

The FD-MS values of the compounds 4-1 to 4-52 of the present inventionprepared according to the above synthesis examples are shown in Table 4below.

TABLE 4 Compound FD-MS Compound FD-MS 4-1 m/z = 639.24(C₄₅H₂₉N₅ =639.75) 4-2 m/z = 715.27(C₅₁H₃₃N₅ = 715.84) 4-3 m/z = 780.33(C₅₇H₄₀N₄ =780.95) 4-4 m/z = 639.24(C₄₅H₂₉N₅ = 639.75) 4-5 m/z = 715.27(C₅₁H₃₃N₅ =715.84) 4-6 m/z = 780.33(C₅₇H₄₀N₄ = 780.95) 4-7 m/z = 612.23(C₄₄H₂₈N₄ =612.72) 4-8 m/z = 612.23(C₄₄H₂₈N₄ = 612.72) 4-9 m/z = 662.25(C₄₈H₃₀N₄ =662.78) 4-10 m/z = 484.19(C₃₆H₂₄N2 = 484.59) 4-11 m/z = 639.24(C₄₅H₂₉N₅= 639.75) 4-12 m/z = 715.27(C₅₁H₃₃N₅ = 715.84) 4-13 m/z =715.27(C₅₁H₃₃N₅ = 715.84) 4-14 m/z = 638.25(C₄₆H₃₀N₄ = 638.76) 4-15 m/z= 579.18(C₄₀H₂₅N₃S = 579.71) 4-16 m/z = 410.14(C₂₉H₁₈N₂S = 410.47) 4-17m/z = 486.17(C₃₅H₂₂N₂O = 486.56) 4-18 m/z = 486.17(C₃₅H₂₂N₂O = 486.56)4-19 m/z = 486.17(C₃₅H₂₂N₂O = 486.56) 4-20 m/z = 563.20(C₄₀H₂₅N₃O =563.65) 4-21 m/z = 460.16(C₃₃H₂₀N₂O = 460.52) 4-22 m/z =536.19(C₃₉H₂₄N₂O = 536.62) 4-23 m/z = 689.26(C₄₀H₃₁N₅ = 689.80) 4-24 m/z= 585.22(C₄₃H₂₇N₃ = 585.69) 4-25 m/z = 610.24(C₄₆H₃₀N₂ = 610.76) 4-26m/z = 610.24(C₄₆H₃₀N₂ = 610.76) 4-27 m/z = 636.26(C₄₈H₃₂N₂ = 636.80)4-28 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 4-29 m/z = 610.24(C₄₆H₃₀N₂ =610.76) 4-30 m/z = 610.24(C₄₆H₃₀N₂ = 610.76) 4-31 m/z = 649.25(C₄₈H₃₁N₃= 649.80) 4-32 m/z = 832.25(C₆₀H₃₆N₂OS = 833.02) 4-33 m/z =560.23(C₄₂H₂₈N₂ = 560.70) 4-34 m/z = 501.16(C₃₆H₂₃NS = 501.65) 4-35 m/z= 435.20(C₃₃H₂₅N = 435.57) 4-36 m/z = 725.28(C₅₄H₃₅N₃ = 725.90) 4-37 m/z= 650.24(C₄₀H₃₀N₂O = 650.78) 4-38 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-39m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-40 m/z = 650.24(C₄₈H₃₀N₂O = 650.78)4-41 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-42 m/z = 666.21(C₄₈H₃₀N₂S =666.84) 4-43 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-44 m/z =666.21(C₄₈H₃₀N₂S = 666.84) 4-45 m/z = 650.24(C₄₀H₃₀N₂O = 650.78) 4-46m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-47 m/z = 650.24(C₄₈H₃₀N₂O = 650.78)4-48 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-49 m/z = 666.21(C₄₈H₃₀N₂S =666.84) 4-50 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-51 m/z =666.21(C₄₈H₃₀N₂S = 666.84) 4-52 m/z = 666.21(C₄₈H₃₀N₂S = 666.84)

Fabrication and Evaluation of Organic Electronic Element [Example 1]Green OLED (a Phosphorescent Host)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention asluminous host material of the light emitting layer. First, an ITO layer(anode) was formed on a glass substrate, and then4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,“2-TNATA”) was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. And4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, “NPD”) wasvacuum-deposited on the hole injection layer to form a hole transportlayer with a thickness of 60 nm.

Subsequently, a light emitting layer with a thickness of 30 nm wasvacuum-deposited on the hole transport layer by using compound 1-1 ofthe present invention as a host material andtris(2-phenylpyridine)-iridium (hereinafter, “Ir(ppy)₃”) as a dopantmaterial in a weight ratio of 95:5.

Subsequently,(1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, andtris-(8-hydroxyquinoline)aluminum (hereinafter, “Alq₃”) wasvacuum-deposited with a thickness of 40 nm on the hole blocking layer toform an electron transport layer.

Next, LiF was deposited with a thickness of 0.2 nm on the electrontransport layer to form an electron injection layer, and then Al wasdeposited with a thickness of 150 nm on the electron injection layer toform a cathode.

[Example 2] to [Example 40] Green OLED

The OLEDs were fabricated in the same manner as described in Example 1except that compounds of the present invention described in Table 5instead of the compound 1-1 of the present invention were used as hostmaterial of a light emitting layer, respectively.

[Comparative Example 1 to [Comparative Example 5]

The OLEDs were fabricated in the same manner as described in Example 1except that one of the comparative compounds A to E of the presentinvention instead of the compound 1-1 of the present invention was usedas host material of a light emitting layer.

Electroluminescence (EL) characteristics were measured with a PR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples 1 to 40 of the present invention and ComparativeExamples 1 to 5. And, the T95 life time was measured using a life timemeasuring apparatus manufactured by Mac science Inc. at referencebrightness of 5000 cd/m². The measurement results are shown in Tables 5below.

TABLE 5 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T (95) x y comp. Ex (1) comp. Com A5.9 21.2 5000.0 23.6 56.1 0.31 0.60 comp. Ex (2) comp. Com B 5.5 18.05000.0 27.8 76.6 0.32 0.63 comp. Ex (3) comp. Com C 5.7 17.4 5000.0 28.772.1 0.30 0.62 comp. Ex (4) comp. Com D 5.3 15.6 5000.0 32.1 84.8 0.310.61 comp. Ex (5) comp. Com E 5.1 13.9 5000.0 35.9 83.7 0.33 0.62 Ex.(1) 1-1 4.2 10.6 5000.0 47.2 105.0 0.34 0.63 Ex. (2) 1-7 4.3 10.3 5000.048.8 103.3 0.34 0.64 Ex. (3) 1-9 4.2 10.3 5000.0 48.5 108.3 0.34 0.64Ex. (4) 1-14 4.2 10.2 5000.0 48.8 102.0 0.34 0.63 Ex. (5) 1-20 4.1 10.25000.0 48.9 104.1 0.33 0.65 Ex. (6) 1-21 4.2 10.6 5000.0 47.3 101.6 0.340.63 Ex. (7) 1-25 4.0 10.1 5000.0 49.7 107.2 0.31 0.61 Ex. (8) 1-26 4.010.6 5000.0 47.1 100.6 0.33 0.63 Ex. (9) 1-27 4.0 10.6 5000.0 47.1 104.10.31 0.62 Ex. (10) 1-28 4.2 10.7 5000.0 46.7 102.5 0.35 0.63 Ex. (11)1-33 4.2 10.0 5000.0 49.8 109.1 0.30 0.60 Ex. (12) 1-34 4.0 10.1 5000.049.4 105.9 0.35 0.61 Ex. (13) 1-35 4.2 10.8 5000.0 46.3 103.8 0.33 0.65Ex. (14) 1-36 4.2 10.7 5000.0 46.7 103.5 0.32 0.64 Ex. (15) 1-51 4.510.9 5000.0 45.9 109.7 0.30 0.64 Ex. (16) 1-56 4.5 10.9 5000.0 45.8105.7 0.31 0.62 Ex. (17) 1-57 4.3 11.3 5000.0 44.1 105.2 0.31 0.64 Ex.(18) 1-62 4.5 11.9 5000.0 42.2 100.2 0.33 0.64 Ex. (19) 1-67 4.6 11.95000.0 42.1 102.1 0.32 0.63 Ex. (20) 1-72 4.6 11.6 5000.0 43.0 106.10.32 0.63 Ex. (21) 1-73 4.6 11.8 5000.0 42.2 105.8 0.33 0.64 Ex. (22)1-75 4.6 11.8 5000.0 42.3 105.6 0.31 0.64 Ex. (23) 1-77 4.6 11.9 5000.042.1 104.1 0.31 0.64 Ex. (24) 2-1 4.5 11.1 5000.0 45.0 105.3 0.34 0.62Ex. (25) 2-6 4.5 11.2 5000.0 44.7 105.8 0.32 0.61 Ex. (26) 2-11 4.4 11.25000.0 44.6 100.1 0.32 0.65 Ex. (27) 2-16 4.4 10.9 5000.0 45.7 102.30.31 0.63 Ex. (28) 2-20 4.5 11.0 5000.0 45.4 101.2 0.34 0.62 Ex. (29)2-23 4.5 10.9 5000.0 46.0 109.1 0.35 0.60 Ex. (30) 2-26 4.4 11.1 5000.045.1 106.6 0.35 0.63 Ex. (31) 2-29 4.4 11.2 5000.0 44.8 101.2 0.35 0.64Ex. (32) 2-34 4.5 10.9 5000.0 45.8 105.4 0.34 0.61 Ex. (33) 2-39 4.511.0 5000.0 45.5 101.1 0.32 0.62 Ex. (34) 2-44 4.5 11.3 5000.0 44.1103.6 0.35 0.60 Ex. (35) 2-45 4.4 11.3 5000.0 44.2 106.8 0.34 0.64 Ex.(36) 2-51 4.6 11.4 5000.0 43.9 102.2 0.31 0.60 Ex. (37) 2-55 4.8 12.05000.0 41.5 105.9 0.34 0.63 Ex. (38) 2-60 4.8 12.3 5000.0 40.6 103.10.32 0.61 Ex. (39) 3-10 4.3 10.4 5000.0 48.3 109.4 0.35 0.60 Ex. (40)3-2 4.9 12.9 5000.0 38.9 98.9 0.33 0.65

From Table 5, it can be seen that when using the compound according toan embodiment of the present invention as a phosphorescent host materialof the light-emitting layer, compared with the case of using one ofComparative Compound A to Comparative Compound E, the driving voltage,the luminous efficiency and lifetime are significantly improved that arethe electrical characteristics of the organic electroluminescent device.Comparative Compound A is CBP generally used as a host material, andComparative Compounds B to E contain triazine and have a skeletonsimilar to that of the compounds of the present invention.

Comparing Comparative Examples 1 to 5, Comparative Examples 2 to 5 havebetter electrical characteristics of the organic electroluminescentdevice than Comparative Example 1, wherein CBP generally used as a hostmaterial is used as a phosphorescent host material of a light emittinglayer in Comparative Example 1, and Comparative Compounds B to E containtriazine and have a skeleton similar to that of the compounds of thepresent invention in Comparative Examples 2 to 5.

On the other hand, comparing the Examples of the present invention andComparative Examples 2 to 5, it can be seen that the driving voltage ofthe organic electric device manufactured according to the embodiment ofthe present invention is lower, and the luminous efficiency and lifespanare significantly improved. This seems to be due to the difference inphysical properties between the compounds of the present invention andComparative Compounds B to E used as phosphorescent host materials.

The compounds of the present invention and Comparative Compounds B to Eare all similar in that they contain triazine and heterocycles areattached to both sides of the triazine.

However, in the compound of the present invention, 1-dibenzofuran or1-dibenzothiophene substituted with an aryl group (corresponding to Ar³in Formula 1) is directly bonded to one side of the triazine (one of thecarbons of the triazine ring), and 4-dibenzofuran or 4-dibenzothiopheneis bonded to the other side (another carbon of the triazine ring) via anarylene group such as phenyl or biphenyl. On the other hand, in the caseof Comparative Compound B, 1-dibenzofuran and 4-dibenzofuran are bothdirectly connected to the carbon of the triazine, in the case ofComparative Compound C, 1-dibenzofuran and 4-dibenzofuran are bothbonded to the triazine through a linking group such as phenyl, inComparative Compounds D and E, 1-dibenzofuran is connected to thetriazine via a phenyl linkage group. The comparative compounds aresimilar to the compound of the present invention in that 4-dibenzofuranis directly connected to the triazine, but the portion corresponding toAr³ is different in that the present invention is substituted with anaryl group, while the comparative compounds are substituted with aheteroaryl group.

Due to such a difference in the structure of the compound, when usingeach of these compounds as a phosphorescent host material, thecharacteristics of the device are different, and the device propertiesof Comparative Examples 4 and 5 were better than those of ComparativeExamples 2 and 3.

Therefore, it can be seen that the device characteristics are furtherimproved in compound in which 1-dibenzofuran is bonded to triazinethrough a linkage group such as phenyl, and 4-dibenzofuran is directlybonded to triazine than in compound in which 1-dibenzofuran and4-dibenzofuran are directly bonded to triazine or they are bonded viaphenyl.

In addition, compared to Comparative Example 4 and Comparative Example5, the driving voltage of the organic electroluminescent devicemanufactured according to the embodiment of the present invention wassignificantly lowered, and the luminous efficiency and lifespan weresignificantly improved. From this, it can be seen that the devicecharacteristics are further improved in case of using compound of thepresent invention in which the substituent substituted on the benzenering of 4-dibenzofuran (or 4-dibenzothiophene) is hydrogen or an arylgroup, compared to case of using compound having a heterocycle as asubstituent.

To determine the cause of this result, the energy levels of ComparativeCompounds B to E and Compounds 1-79 of the present invention werecompared as shown in FIGS. 2 and 3.

FIG. 2 is a diagram comparing the energy levels of the comparativeexample compound and the example compound of the present invention.

Referring to FIG. 2, Comparative Compound B and C are classified intoGroup 1, Comparative Compound D and E are classified into Group 2, andCompound 1-79 of the present invention is classified into Group 3.

Group 1 is a group of compounds in which a substituent other thanhydrogen is not bonded to dibenzofuran directly or indirectly attachedto triazine, Group 2 is a group of compounds in which a heterocyclicgroup such as carbazole is substituted in the benzene ring ofdibenzofuran which dibenzofuran is indirectly bound to a triazinethrough a linking group, and Group 3 is a group of compounds in which anaryl group such as phenyl is bonded to a benzene ring of dibenzofuranwhich is indirectly linked via a linking group to a triazine.

Referring to FIG. 2, the LUMO values and the T1 values of Groups 1 to 3do not show significant differences in all three groups, while the HOMOvalues show great differences. It can be seen that the HOMO value of thecompound of Group 3 in which dibenzofuran is substituted with an aryl islarger than that of Group 1 in which dibenzofuran is substituted withhydrogen only.

Therefore, from these results, the HOMO energy level of the compound canbe significantly changed according to the type of the substituentattached to the benzene ring of dibenzofuran, and the difference inphysical properties of these compounds affects device performance indepositing the compound during device fabrication and it suggests thatsince it acts as a main factor (for example, energy balance, chargebalance, etc.), device characteristics such as driving voltage, luminousefficiency, and lifetime may vary.

On the other hand, FIG. 3 is a view comparing the band gap (band gap) ofthe comparative example compound and the compound of the presentinvention.

In FIG. 3, the band gap values are divided into two groups according tothe characteristics of each compound, and the first group to whichComparative Compound B and C belong and the second group to whichComparative Compounds D, E and Compound 1-79 of the present inventionbelong are divided.

In the compound belonging to the first group, all dibenzofurans aredirectly connected to the triazine or both are indirectly connectedthrough a phenylene linking group, while in the compound belonging tothe second group, dibenzofuran is directly connected to one side of thetriazine and indirectly to the other side through a linking group suchas phenylene.

Referring to FIG. 3, Group 1 has a band gap of approximately 4.0 eV,while Group 2 has a band gap of approximately 3.4 eV, and the two groupshave significant differences in band gap.

Therefore, it can be seen that the energy level (band gab) of thecompound may vary depending on the form of the combination of triazineand dibenzofuran, and the difference in physical properties affectsdevice performance when depositing the compound during devicemanufacturing. It can be seen that different device characteristics canbe derived by changing the main factors (eg, energy balance or chargebalance).

In conclusion, referring to FIGS. 2 and 3, it can be seen that thecompounds of the present invention differ from the comparative compoundsin HOMO value and band gap, wherein the inventive compound has1-dibenzofuran (or 1-dibenzothiophene) on one side of a triazine via alinking group such as an arylene group and 4-dibenzofuran (or4-dibenzothiophene) substituted with an aryl group on the other side ofa triazin. Due to this difference, the characteristics of the device aresignificantly improved when the compound of the present invention isused as a phosphorescent host material.

[Example 41] to [Example 96] Green OLED (Phosphorescent Host Mixture)

The OLEDs were fabricated in the same manner as described in Example 1except that a mixture of two kinds of compounds of the present inventionin a weight ratio of 6:4 was used as host material of a light emittinglayer as shown in Table 6 below, instead of using compound 1-1 of thepresent invention alone.

[Example 6] to [Example 9] Green OLED (Phosphorescent Host Mixture)

The OLEDs were fabricated in the same manner as described in Example 1except that a mixture of one of Comparative Compounds B to ComparativeCompound E and Compound 4-27 of the present invention in a weight ratioof 6:4 was used as host material of a light emitting layer as shown inTable 6 below, instead of using compound 1-1 of the present inventionalone.

Electroluminescence (EL) characteristics were measured with a PR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples 41 to 96 of the present invention and ComparativeExamples 6 to 9. And, the T95 life time was measured using a life timemeasuring apparatus manufactured by Mac science Inc. at referencebrightness of 5000 cd/m². The measurement results are shown in Tables 6below.

TABLE 6 Current Voltage Density Brightness Efficiency Lifetime Host 1Host 2 (V) (mA/cm²) (cd/m²) (cd/A) T (95) comp. Ex (6) comp. Com B 4-275.4 17.8 5000.0 28.1 110.8 comp. Ex (7) comp. Com C 5.6 17.1 5000.0 29.3113.9 comp. Ex (8) comp. Com D 5.0 14.5 5000.0 34.5 113.0 comp. Ex (9)comp. Com E 4.9 13.4 5000.0 37.3 115.0 Ex. (41) 1-1 4-27 3.6 10.0 5000.049.9 117.5 Ex. (42) 1-7 3.7 10.1 5000.0 49.4 116.1 Ex. (43) 1-9 3.6 10.15000.0 49.5 119.2 Ex. (44) 1-21 3.7 10.0 5000.0 49.8 115.4 Ex. (45) 1-283.6 10.1 5000.0 49.4 117.7 Ex. (46) 1-35 3.7 10.1 5000.0 49.3 116.3 Ex.(47) 1-48 3.6 10.2 5000.0 49.2 115.1 Ex. (48) 1-1 4-25 3.6 10.0 5000.049.9 117.6 Ex. (49) 1-7 3.7 10.2 5000.0 49.2 116.8 Ex. (50) 1-9 3.7 10.15000.0 49.5 117.1 Ex. (51) 1-21 3.7 10.1 5000.0 49.5 118.0 Ex. (52) 1-283.7 10.1 5000.0 49.3 115.1 Ex. (53) 1-35 3.7 10.0 5000.0 49.9 115.9 Ex.(54) 1-48 3.7 10.0 5000.0 49.9 117.4 Ex. (55) 1-1 4-30 3.7 10.0 5000.049.9 116.1 Ex. (56) 1-7 3.7 10.1 5000.0 49.3 116.8 Ex. (57) 1-9 3.6 10.25000.0 49.2 118.9 Ex. (58) 1-21 3.6 10.1 5000.0 49.6 119.9 Ex. (59) 1-283.7 10.2 5000.0 49.2 117.8 Ex. (60) 1-35 3.7 10.1 5000.0 49.5 119.9 Ex.(61) 1-48 3.6 10.1 5000.0 49.5 119.6 Ex. (62) 1-1 4-31 3.5 9.9 5000.050.5 124.1 Ex. (63) 1-7 3.5 9.9 5000.0 50.4 120.7 Ex. (64) 1-9 3.5 10.05000.0 50.1 120.3 Ex. (65) 1-21 3.5 9.9 5000.0 50.7 120.9 Ex. (66) 1-283.4 9.9 5000.0 50.3 121.9 Ex. (67) 1-35 3.5 9.9 5000.0 50.7 121.3 Ex.(68) 1-48 3.4 9.9 5000.0 50.3 123.4 Ex. (69) 1-1 4-37 3.8 10.3 5000.048.4 111.2 Ex. (70) 1-7 3.7 10.3 5000.0 48.6 110.5 Ex. (71) 1-9 3.8 10.45000.0 48.0 113.7 Ex. (72) 1-21 3.8 10.3 5000.0 48.4 113.4 Ex. (73) 1-283.7 10.3 5000.0 48.5 110.5 Ex. (74) 1-35 3.7 10.4 5000.0 48.3 113.2 Ex.(75) 1-48 3.8 10.4 5000.0 48.2 113.3 Ex. (76) 1-1 4-42 3.8 10.4 5000.048.1 114.2 Ex. (77) 1-7 3.7 10.3 5000.0 48.6 113.1 Ex. (78) 1-9 3.8 10.35000.0 48.6 111.6 Ex. (79) 1-21 3.8 10.2 5000.0 48.9 113.9 Ex. (80) 1-283.8 10.3 5000.0 48.8 112.8 Ex. (81) 1-35 3.7 10.2 5000.0 48.9 110.2 Ex.(82) 1-48 3.7 10.3 5000.0 48.7 113.2 Ex. (83) 1-1 4-47 3.8 10.3 5000.048.4 110.0 Ex. (84) 1-7 3.8 10.2 5000.0 48.9 115.0 Ex. (85) 1-9 3.7 10.35000.0 48.5 113.0 Ex. (86) 1-21 3.8 10.4 5000.0 48.1 112.2 Ex. (87) 1-283.8 10.3 5000.0 48.5 114.6 Ex. (88) 1-35 3.7 10.4 5000.0 48.1 110.5 Ex.(89) 1-48 3.8 10.3 5000.0 48.7 113.2 Ex. (90) 1-1 4-52 3.7 10.2 5000.048.8 110.4 Ex. (91) 1-7 3.7 10.4 5000.0 48.1 113.2 Ex. (92) 1-9 3.7 10.35000.0 48.4 113.3 Ex. (93) 1-21 3.8 10.4 5000.0 48.1 113.1 Ex. (94) 1-283.8 10.3 5000.0 48.4 113.1 Ex. (95) 1-35 3.8 10.3 5000.0 48.4 110.8 Ex.(96) 1-48 3.8 10.3 5000.0 48.5 111.1

From Table 6, it can be seen that the driving voltage and the luminousefficiency of the organic electroluminescent device manufacturedaccording to the embodiment of the present invention are significantlyimproved and the lifetime is also improved as compared to thecomparative example. That is, when a mixture of a compound representedby Formula 1 of the present invention as a first host component and acompound represented by Formula 11 of the present invention as a secondhost component is used as host material, compared to a mixture using oneof Comparative Compounds B to E as a first host component and a compoundrepresented by Formula 11 of the present invention as a second hostcomponent, device characteristics of the organic electroluminescentdevice are significantly improved.

From these results, it can be seen that as in the case where thecompound represented by Formula 1 of the present invention is used aloneas a host material, even when a mixture of the compound represented bythe formula 1 of the present invention and the compound represented bythe formula 11 of the present invention is used as a host material, thedriving voltage, luminous efficiency and lifetime of the device aresignificantly improved.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications can be made without departing fromthe essential characteristics of the present invention. Therefore, theembodiments disclosed in the present invention are intended toillustrate the present invention, and the scope of the present inventionis not limited by the embodiments. The scope of the present inventionshall be construed on the basis of the accompanying claims, and it shallbe construed that all of the technical ideas included within the scopeequivalent to the claims belong to the present invention.

1. A compound of Formula 1:

wherein: X¹ and X² are each independently O or S, Ar¹ to Ar² are eachindependently a C₆-C₆₀ aryl group, R¹ to R⁵ are each independentlyselected from the group consisting of hydrogen, deuterium, halogen, aC₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a C₃-C₆₀ aliphatic ring, a fused ring group formedby a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxylgroup, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), and adjacentgroups may be optionally linked to each other to form a ring, whereinthe ring is selected from the group consisting of a C₆-C₆₀ aromaticring, a C₂-C₆₀ heterocyclic group, a C₃-C₆₀ aliphatic ring, and a fusedring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromaticring, a and b are each an integer of 0 to 3, c, d, e, l and m are eachan integer of 0 to 4, and n is an integer of 1 to 5, L′ is selected fromthe group consisting of a single bond, a C₆-C₆₀ arylene group, afluorenylene group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₆₀ aliphatic ring and a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, R_(a) and R_(b) are eachindependently selected from the group consisting of a C₆-C₆₀ aryl group,a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₆₀ aliphatic ring and a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, Ar¹ to Ar³, R¹ to R⁵, L′,R_(a), R_(b), and a ring formed by bonding neighboring groups among R¹to R⁵ to each other may be each further substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or aC₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a phosphine oxide group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkyl group, afused ring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group.2. The compound of claim 1, wherein Formula 1 is represented by one ofFormula 2 to Formula 5:

wherein Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, l, m and n are the same asdefined in claim
 1. 3. The compound of claim 1, wherein Formula 1 isrepresented by one of Formula 6 to Formula 8:

wherein X¹, X², Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, l and m are thesame as defined in claim
 1. 4. The compound of claim 1, wherein Formula1 is represented Formula 9 or Formula 10:

wherein X¹, X², Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, m and n are thesame as defined in claim
 1. 5. The compound of claim 1, wherein Formula1 is represented by one of Formula 11 to Formula 13:

wherein X¹, X², Ar¹ to Ar³, R¹, R², R⁴, R⁵, a, b, d, e, l, m and n arethe same as defined in claim
 1. 6. The compound of claim 1, whereinFormula 1 is represented by Formula 14:

wherein, X¹, X², Ar¹ to Ar³, R¹ to R⁵, a, b, c, d, e, l and m are thesame as defined in claim
 1. 7. The compound of claim 1, wherein at leastone of Ar¹, Ar³ and R³ is a C₆-C₂₄ aryl group.
 8. The compound of claim1, wherein Ar¹ or Ar³ is a C₆-C₂₄ aryl group.
 9. The compound of claim1, wherein R³ is a C₆-C₂₄ aryl group.
 10. The compound of claim 1,wherein the compound represented by Formula 1 is one of the followingcompounds:


11. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises a single compound or two or more compounds represented by theFormula
 1. 12. The organic electric element of claim 11, wherein theorganic material layer comprises at least one layer of a hole injectionlayer, a hole transport layer, an emission-auxiliary layer, a lightemitting layer, an electron transport auxiliary layer, an electrontransport layer and an electron injection layer.
 13. The organicelectric element of claim 12, wherein the compound is comprised in thelight emitting layer.
 14. The organic electric element of claim 13,wherein the light emitting layer further comprises compound representedby the following Formula 15:

wherein, Z¹ to Z⁴, Z¹³ to Z¹⁶ are independently C(R) or N, Z⁵ to Z¹² areindependently C, C(R) or N, L² is selected from the group consisting ofa single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring and afused ring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring, W is N(Ar⁵), O, S or C(R′)(R″), Ar⁴ and Ar⁵ are eachindependently selected from the group consisting of a C₆-C₆₀ aryl group,a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₆₀ aliphatic ring, a fused ring group formed by a C₃-C₆₀ aliphaticring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenylgroup, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxygroup, -L′-N(R_(a))(R_(b)) and a combination thereof, R, R′ and R″ areeach independently selected from the group consisting of hydrogen,deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring, a fusedring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromaticring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and-L′-N(R_(a))(R_(b)), adjacent R groups may be optionally linked to eachother to form a ring, and R′ and R″ may be optionally linked to eachother to form a ring, wherein the ring is selected from the groupconsisting of a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic group, aC₃-C₆₀ aliphatic ring, and a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring, L′, R_(a) and R_(b) are thesame as defined in claim 1, Z¹ to Z¹⁶, L², Ar⁴, Ar⁵, R, R′, R″, a ringformed by linking between adjacent R groups, and a ring formed bylinking between R′ and R″ may be each further substituted with one ormore substituents selected from the group consisting of deuterium,halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkylgroup or a C₆-C₂₀ aryl group, a siloxane group, a boron group, agermanium group, a cyano group, a nitro group, a phosphine oxide groupunsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ arylgroup, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ arylgroup, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenylgroup, a C₂-C₂₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P, a C₃-C₂₀cycloalkyl group, a fused ring group formed by a C₃-C₆₀ aliphatic ringwith a C₆-C₆₀ aromatic ring, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group.
 15. The organic electric element of claim 14, whereinFormula 15 is represented by one of Formulas 16 to 19:

wherein, Ar⁴, Ar⁵, Z¹ to Z¹⁶, L², R′ and R″ are the same as defined inclaim
 14. 16. The organic electric element of claim 14, wherein both Ar⁴and Ar⁵ are a C₆-C₃₀ aryl group.
 17. The organic electric element ofclaim 14, wherein Formula 15 is represented by Formula 20:

wherein, Ar⁴, Z¹ to Z¹⁶, and L² are the same as defined in claim 14, Yis O, S or N(R^(c)), L¹ is selected from the group consisting of asingle bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring and afused ring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring, R^(a) and R^(b) are each independently selected from thegroup consisting of hydrogen, deuterium, halogen, a C₆-C₂₀ aryl group, afluorenyl group, a C₆-C₂₀ aryl group substituted with deuterium, aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkylgroup, a fused ring group formed by a C₃-C₆₀ aliphatic ring with aC₆-C₆₀ aromatic ring, a C₇-C₂₀ arylalkyl group and a C₈-C₂₀ arylalkenylgroup, and adjacent groups may be optionally linked to each other toform a ring, wherein the ring is selected from the group consisting of aC₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic group, a C₃-C₆₀ aliphaticring, and a fused ring group formed by a C₃-C₆₀ aliphatic ring with aC₆-C₆₀ aromatic ring, R^(c) is selected from the group consisting of aC₆-C₂₀ aryl group, a fluorenyl group, a C₆-C₂₀ aryl group substitutedwith deuterium, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₂₀ cycloalkyl group, a fused ring group formed by a C₃-C₆₀ aliphaticring with a C₆-C₆₀ aromatic ring and a combination thereof, y is aninteger of 0 to 3, z is an integer of 0 to 4, where each of these is aninteger of 2 or more, each of R^(a)s, each of R^(b)s is the same ordifferent from each other,
 18. The organic electric element of claim 14,wherein the compound represented by Formula 15 is one of the followingcompounds:


19. The organic electric element of claim 11, wherein the organicmaterial layer is formed by one of the processes of spin coating, nozzleprinting, inkjet printing, slot coating, dip coating and roll-to-roll.20. An electronic device comprising a display device and a control unitfor driving the display device, wherein the display device comprises theorganic electric element of claim
 11. 21. The electronic device of claim20, wherein the organic electric element is one of an organic lightemitting diode, an organic solar cell, an organic photo conductor, anorganic transistor, and an element for monochromatic or whiteillumination.